Triazine derivative and a herbicide comprising the same as an effective ingredient

ABSTRACT

A triazine compound of the formula  &lt;IMAGE&gt;  wherein Y1 is a hydrogen atom or a methyl group and Z is an oxygen atom or a sulfur atom, X1 is a halogen atom and R is a hydrogen atom, a methyl group or an ethyl group. The triazine compound is useful as a herbicide for combatting weeds.

This is a division of application Ser. No. 07/582,835 filed Oct. 5,1990, which is the United States designated application ofPCT/JP90/00194 filed Feb. 19, 1990, now U.S. Pat. No. 5,290,754 issuedMar. 1, 1994.

FIELD OF TECHNOLOGY

The present invention relates to novel triazine derivatives and aherbicide containing the derivatives as an effective ingredient.

BACKGROUND TECHNOLOGY

A variety of herbicides have been hitherto developed and contributed tothe productivity and labor-saving in agriculture. However, certain kindsof herbicides have been used over so long years that population oftroublesome weeds withstanding them are increasing so that appearance isdesired of a herbicids having a broad herbicidal spectrum andeffectiveness also against these troublesome weeds. It is also desiredto develop a high-activity herbicide in order to overcome the problem ofenvironmental pollution by conventional herbicides. In order to overcometo the problem of the ununiform germination of weeds over a long periodof time, furthermore, appearance is also awaited of a herbicideexhibiting excellent persistent effectiveness and having a versatilityof treatment to exhibit effectiveness even by treatment over a widerange of period from the pre-germination stage to the growing period ofweeds.

The inventors have continued investigations to develop a herbicidecapable of exhibiting an excellent herbicidal effect against variouskinds of annual and perennial weeds without causing phytotoxicity topaddy rice and arrived at a discovery that a herbicide containing atriazine compound as an effective ingredient is effective (officialpublication of Japanese Patent Toku-sai-hyo 88/02368, officialpublication of Japanese Patent Kokai 63-146876, official publication ofJapanese Patent Kokai 63-51379 and official publication of JapanesePatent Kokai 63-264465). This triazine-based herbicide is highly activeagainst troublesome weeds in paddy rice field at low dosage withoutphytotoxicity to-paddy rice plant. This herbicide also shows excellentherbicidal activity against troublesome weeds by foliage application inupland field without phytotoxicity to Gramineous crops.

Nevertheless, this herbicide shows somewhat limited performance bypreemergence treatment to the soil in upland fields.

DISCLOSURE OF THE INVENTION

The present invention provides:

(1) a triazine derivative represented by the general formula ##STR2##[in the formula, A denotes ##STR3## (in which Y¹ denotes a hydrogen atomor a methyl group and Z denotes an oxygen atom or a sulfur atom),##STR4## (in which Y² and Y³, which can be of the same kind or differentkinds each denote a methyl group or a methoxy group) or ##STR5## (inwhich Y⁴ denotes a methyl group, trifluoromethyl group, methoxy group orfluorine atom and n denotes an integer of 0 to 2), X¹ denotes a halogenatom and R¹ denotes hydrogen, a methyl group or an ethyl group], and

(2) a herbicide containing, as an effective ingredient, a triazinederivative represented by the general formula ##STR6## [in the formula,A denotes ##STR7## (in which Y¹ denotes a hydrogen atom or a methylgroup and Z denotes an oxygen atom or a sulfur atom), ##STR8## (in whichY² and Y³, which can be of the same kind or different kinds, each denotea methyl group or a methoxy group) or ##STR9## (in which Y⁴ denotes amethyl group, trifluoromethyl group, methoxy group or fluorine atom andn denotes an integer of 0 to 2), X¹ denotes a halogen atom and R¹denotes hydrogen, a methyl group or an ethyl group].

The inventors have continued investigations to search a compound freefrom phytotoxicity to the crops of the family of Gramineae in uplandfields capable of exhibiting a high herbicidal effect againsttroublesome weeds both in the treatment to soil and in the treatment tofoliage with an excellent effect of soil treatment in paddy fields. As aresult, a discovery has been reached that those having a specifichaloalkyl group are effective leading to completion of the presentinvention.

The triazine derivative of the present invention is a novel compound andcan be effectively utilized as a herbicide. When used as a herbicide forupland fields, the herbicide of the present invention containing thetriazine derivative as an effective ingredient can be used over a longterm for appropriate chemical treatment as compared with existingherbicides for upland fields and exhibits a high activity againsttroublesome weeds both in the soil treatment before germination and inthe course of germination of the weeds and in the foliage treatmentduring the growth period of the weeds still without phytotoxicity tocrops. In particular, a remarkably high effect is obtained by the soiltreatment or treatment to foliage in non-paddy fields of crops belongingto Gramineous crops. As compared with existing herbicides for paddyrice, in addition, the herbicide of the present invention has a highchemical effect against hardly eliminable weeds still with littlephytotoxicity.

BEST MODE TO PRACTICE THE INVENTION

The present invention provides a triazine derivative represented by thegeneral formula ##STR10## [in the formula, A denotes ##STR11## (in whichY¹ denotes a hydrogen atoms or a methyl group and Z denotes an oxygenatom or a sulfur atom), ##STR12## (in which Y² and Y³, which can be ofthe same kind or of different kinds, each denote a methyl group or amethoxy group) or ##STR13## (in which Y⁴ denotes a methyl group,trifluoromethyl group, methoxy group or fluorine atom and n denotes aninteger of 0 to 2), X¹ denotes a halogen atom and R¹ denotes hydrogen, amethyl group or an ethyl group] and also provides a herbicide containingthe triazine derivative represented by the above given general formula[I] .

The triazine derivative of the present invention represented by theabove given general formula [I] can be prepared by various differentmethods. The method of preparation with the highest efficiency amongthem is the method to react an alkyl amine salt represented by thegeneral formula ##STR14## [in the formula, A is the same as given aboveand X³ denotes a halogen atom] and cyanoguanidine expressed by theformula ##STR15## to prepare an alkyl biguanide salt represented by thegeneral formula ##STR16## [in the formula, A and X³ are each the same asgiven above] and then to react the alkyl biguanide salt with an alkylester represented by the general formula ##STR17## [in the formula, R¹and X¹ are each the same as given above and R² denotes an alkyl grouphaving 1 to 4 carbon atoms]. In this manner, the alkyl amine saltrepresented by the general formula [II] and cyanoguanidine are reactedto give the alkyl biguanide salt represented by the general formula[III] which is reacted with the alkyl ester represented by the generalformula [IV] to give the desired triazine derivative represented by thegeneral formula [I] in high efficiency.

In conducting the reaction between the alkyl amine salt represented bythe above given general formula [II] and cyanoguanidine here, these twocompounds can be used in an approximately equimolar proportion andusable solvents include cyclic hydrocarbons such as benzene, Decalin,alkyl naphthalenes and the like and chlorinated hydrocarbons such ascarbon tetrachloride, ethylene dichloride, chlorobenzene,dichlorobenzene, trichlorobenzene and the like. And, the reactiontemperature is not particularly limitative and sufficient proceeding canbe obtained in the range from low to high temperatures or, inparticular, from 80° to 200° C.

The salt of an alkyl biguanide derivative represented by the generalformula [III] is obtained by this reaction and, in the method of thepresent invention, this is reacted with the alkyl ester of the generalformula [IV] ##STR18## prepare the desired triazine derivativerepresented by the general formula [I]. This reaction usually proceedsin high efficiency at about 10° to 100° C. in the presence of a catalystsuch as a base and the like in a solvent such as alcohols, e.g.,methanol, ethanol, isopropanol and the like, various kinds of ketones,aliphatic hydrocarbons, various kinds of ethers, various kinds of cyclichydrocarbons, chlorinated hydrocarbons and the like.

The triazine derivatives of the general formula [I] obtained by theabove described method are each a novel compounds.

And, the compound of the present invention has optical isomers and isobtained usually as a racemic modification while it is possible toobtain the respective antipodes by a known method such as asymmetricsynthesis. The compound of the present invention can be used as aherbicide either in the form of the racemic modification or in the formof the isolated optical isomer. Furthermore, the compound of the presentinvention also can be used as a herbicide in the form of a salt of aninorganic acid or organic acid.

Furthermore, the triazine derivative represented by the general formula[I] inhibits germination and growth of weeds and has high selectivity sothat it is satisfactory as a herbicide. In addition, it is useful notonly for the soil treatment before the germination of weeds as a matterof course but also for the foliage treatment to the growing weeds tohave a versatility of the chemical treatment. The triazine derivative ofthe present invention exhibits no phytotoxicity to the crops belongingto Gramineous crops such as corn, grain sorghum, wheat, barley, oat andthe like as the important crops in upland fields and exhibits aprominent herbicidal effect against strongly troublesome broadleaf weedssuch as Cassia obtusifolia L., Ipomoea purpurea, Abutilon theophrasti,Galium sparium var. echincsoermcn, Stellaria media, Veronica persica,Polygonurn persicaria, Viola arvensis, Brassica juncea, Amaranthuspatulus, Common blackjack and the like and strongly harmful weedsbelonging to the family of Graminea such as Digitaria sanguinalis,Alopecurus myosuroides and the like.

Furthermore, this triazine derivative not only exhibits a prominentherbicidal effect against broadleaf weeds such as Rotala indica (Willd)Koehne var. uligirosa (Miq.) Koehne, Lindernia pyxidaria L., Monochoriavaginalis Presl var. plantaginea and the like, weeds belonging to thefamily of Cyperaceae such as Cyperus difformis L. and the like and weedsbelonging to the family of Gramineae such as Echinochloa crus-galli P.Beauv. vat. formosensis Ohwi and the like but also exhibits a prominentherbicidal effect against perennial weeds such as Scirpus juncoidesRoxb. ssp. Hotarui Ohwi T. Koyama, Cyperus serotinus Rottb., Sagittariapygmaea Miq. and the like, which are currently deemed to be hardlyeliminable, without causing chemical damages against paddy rice.

In the next place, the herbicide of the present invention contains theabove described compound or, namely, the triazine derivative representedby the general formula [I] as the effective ingredient and thesecompounds can be used as being prepared in the preparation form such asa water-dispersible powder, emulsion, dust, granules, flowable agent,solution and the like by mixing with a liquid carrier such as solventsand the like or a solid carrier such as mineral fine powders and thelike. In the preparation of the form, it is optional according to needto add an emulsifying agent, dispersion aid, spreading agent, suspendingagent, penetrating agent, stabilizer and other adjuvants.

When the herbicide of the present invention is used in the form of awater-dispersible powder, usually, a composition to be used is preparedby compounding from 10 to 55% by weight of the above described triazinederivative of the present invention as the effective ingredient, from 40to 88% by weight of a solid carried and from 2 to 5% by weight of asurface active agent. Further, when it is used in the form of anemulsion or a flowable agent, it can be usually prepared by compoundingfrom 5 to 50% by weight of the triazine derivative of the presentinvention as the effective ingredient, from 35 to 90% by weight of asolvent and a surface active agent and from 5 to 15% by weight of otheradjuvants.

When it is used in the form of a dust, on the other hand, it can beprepared usually by compounding from 1 to 15% by weight of the triazinederivative of the present invention as the effective ingredient and from85 to 99% by weight of a solid carrier. When it is used in the form ofgranules, furthermore, they can be prepared usually by compounding from0.1 to 15% by weight of the triazine derivative of the present inventionas the effective ingredient, from 80 to 97.9% by weight of a solidcarrier and from 2 to 5% by weight of a surface active agent. The solidcarrier used here is a fine mineral powder and such a fine mineralpowder includes diatomaceous earth, oxides such as hydrated lime and thelike, phosphates such as apatite and the like, sulfates such as gypsumand the like, silicates such as talc, pyrophyllite, clay, kaolin,bentonitc, acid clay, white carbon, quartz powder, silica stone powderand the like, and so on.

And, the liquid carrier includes organic solvents such as paraffinic ornaphthenic hydrocarbons, e.g., kerosine, mineral oil, spindle oil andthe like, aromatic hydrocarbons, e.g., benzene, toluene, xylene and thelike, chlorinated hydrocarbons, e.g., 2-chlorotoluene, trichloromethane,trichloroethylene and the like, alcohols, e.g., cyclohexanol, amylalcohol, ethylene glycol and the like, alcohol ethers, e.g., ethyleneglycol monomethyl ether, ethylene glycol monoethyl ether and the like,ketones, e.g., isophorone, cyclohexanone, cyclohexenyl cyclohexanone andthe like, ethers, e.g., Butyl Cellosolve, dimethyl ether, methyl ethylether and the like, esters, e.g., isopropyl acetate, benzyl acetate,methyl phthalate and the like, amides e.g., dimethyl formamide and thelike, nitriles, e.g., acetonitrile, propionitrile and the like, andsulfoxides, e.g., dimethyl sulfoxide and the like as well as mixturesthereof, water and the like.

Further, as the surface active agent, any one can be used among theanionic type ones (alkylbenzene sulfonates, alkyl sulfonates, lauricacid amide sulfonate and the like), nonionic type ones (polyoxyethyleneoctyl ether, polyethylene glycol laurate, sorbitan alkyl esters and thelike), cationic type ones (dimethyl lauryl benzyl ammonium chloride,lauryl amine, stearyl trimethyl ammonium chloride and the like) andamphoteric type ones (amino acids, betaine and the like).

Further, it is optional with an object to improve the nature of thepreparation form and to enhance the herbicidal effect that the compoundof the present invention is used in combination with a polymericcompound or adjuvant such as sodium alginate, carboxymethyl cellulose,carboxy vinyl polymer, gum arabic, hydroxypropyl methyl cellulose andthe like.

The above described triazine derivative of the present invention as anovel compound represented by the general formula [I] exhibits anexcellent effect as a high-selectivity herbicide not causing anyphytotoxicity for the crops in non-paddy fields such as corn, grainsorghum, wheat, barley, oat and the like by the soil treatment orfoliage treatment either before germination or after germination ofweeds. And, the herbicidal effect is high not only against annual weedsas a matter of course but also against perennial weeds and it is veryuseful as a high-selecte herbicide not causing any phytotoxicity alsofor paddy rice.

The herbicide of the present invention is administered in a dose ofapproximately from 0.1 to 1000 g or, preferably, from 1 to 100 g per 10ares as the effective ingredient. When it is applied on foliage ofplants, it is administered as being diluted to about 1 to 10000 ppm or,preferably, to 10 to 1000 ppm.

Incidentally, it is optional to use the triazine derivative representedby the general formula [I] in combination with other herbicidalconstituents as the effective ingredient of the herbicide of the presentinvention. Such an auxiliary herbicidal constituent can be a herbicidehitherto on the market including various ones exemplified, for example,by the phenoxy-type herbicides, diphenyl ether-type herbicides,triazine-type herbicides, urea-type herbicides, carbamate-typeherbicides, thiol carbamate-type herbicides, acid anilide-typeherbicides, pyrazole-type herbicides, phosphoric acid-type herbicides,sulfonyl urea-type herbicides, nitrile-type herbicides,dinitroaniline-type herbicides, imidazolinone-type herbicides,oxadiazone and the like.

Furthermore, the herbicide of the present invention can be used asmixture with insecticides, germicides, growth-controlling agents ofplants, fertilizers and the like according to need.

EXAMPLES

In the following, the present invention is described in further detailby way of examples.

PREPARATION EXAMPLE 1

Sodium methoxide was produced by gradually adding 0.92 g (40 m moles) ofsodium to 20 ml of dried methanol and 2-(3',5'-dimethylphenoxy)isopropyl biguanide hydrochloride (20 m moles) (described in theofficial publication of Japanese Patent Kokai No. 63-264465) as thestarting material I was added thereto and agitated for 30 minutes atroom temperature. In the next place, 4.80 ml (40 m moles) of ethyl esterof α-fluoro-α-methyl propionic acid as the starting material II wereadded dropwise and agitated for 10 hours at room temperature. Aftercompletion of the reaction, the content material was poured into 100 mlof water and subjected to three times of extraction with 50 ml of ethylacetate. This ethyl acetate layer was dried with anhydrous sodiumsulfate followed by removal of the ethyl acetate by distillation underreduced pressure. The residue was purified by the silica gel columnchromatography (developing solvent: hexane/ethyl acetate=4/1) followedby recrystallization from hexane-ethyl ether to give white2-amino-4-[2-(3', 5'-dimethylphenoxy) isopropylamino]-6-fluoroisopropyl-s-triazine (compound I). The produced amount, %yield, results of analysis, structural formula and others thereof areshown in Tables 1 to 3.

PREPARATION EXAMPLES 2 to 41

Compounds 2 to 41 were obtained by conducting the same procedure as inPreparation Example 1 excepting the use of 20 m moles of the alkylbiguanide hydrochloride (described in the official publication ofJapanese Patent Toku-Sai-Hyo No. 88/02368, official publication ofJapanese Patent Kokai No. 63-51379 and official publication of JapanesePatent Kokai No. 63-264465) indicated in Table 1 in place of the2-(3',5'-dimethylphenoxy) isopropyl biguanide hydrochloride as thestarting material I in Preparation Example 1 and the use of 20 m molesof the ester indicated in Table 1 in place of the ethyl ester ofα-fluoro-α-methyl propionic acid as the starting material II. Theproduced amounts, % yields, results of analysis, structural formulas andothers of these compounds are shown in Tables 1 to 3.

                                      TABLE 1                                     __________________________________________________________________________                                         Results of Analysis (%)                  Preparation                          Melting                                                                            Elementary Analysis                 Example No.                                                                            Starting Materials  Yield                                                                             Yield                                                                             Point                                                                              (%)                                 (Compound No.)                                                                         I         II        (g) (%) (°C.)                                                                       C   H  N                            __________________________________________________________________________    Preparation                                                                            2-(3',5'-dimethyl-                                                                      α-fluoro, α-methyl                                                          2.53                                                                              38  102.4-                                                                             53.9                                                                              7.3                                                                              21.0                         Example 1                                                                              phenoxy)-1-methyl-                                                                      propionic acid    104.9                                                                              (61.2)                                                                            (7.3)                                                                            (21.0)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester                                                No. 1)                                                                        Preparation                                                                            2-(3',5'-dimethyl-                                                                      α-fluoro-propionic                                                                0.83                                                                              13  Color-                                                                             60.0                                                                              7.1                                                                              22.3                         Example 2                                                                              phenoxy)-1-methyl-                                                                      acid n-butyl ester                                                                              less,                                                                              (60.2)                                                                            (6.9)                                                                            (21.9)                       (Compound                                                                              ethyl biganide              resinous                                 No. 2)                                                                        Preparation                                                                            2-(3',5'-dimethyl-                                                                      α-chloro                                                                          1.61                                                                              24  Color-                                                                             56.2                                                                              6.7                                                                              21.2                         Example 3                                                                              phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (57.2)                                                                            (6.6)                                                                            (20.9)                       (Compound                                                                              ethyl biganide                                                                          methyl ester      resinous                                 No. 3)                                                                        Preparation                                                                            2-(2',3'-dimethyl-                                                                      α-fluoro, α-methyl                                                          2.80                                                                              42  134.5-                                                                             60.9                                                                              7.1                                                                              21.2                         Example 4                                                                              phenoxy)-1-methyl-                                                                      propionic acid    136.0                                                                              (61.2)                                                                            (7.3)                                                                            (21.0)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester                                                No. 4)                                                                        Preparation                                                                            2-(2',5'-dimethyl-                                                                      α-fluoro, α -methyl                                                         2.27                                                                              34  Color-                                                                             63.0                                                                              7.4                                                                              21.1                         Example 5                                                                              phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (61.2)                                                                            (7.3)                                                                            (21.0)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 5)                                                                        Preparation                                                                            2-(2',5'-dimethyl-                                                                      α-chloro, α-methyl                                                          1.06                                                                              15  Color-                                                                             59.0                                                                              6.7                                                                              20.4                         Example 6                                                                              phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (58.4)                                                                            (6.9)                                                                            (20.0)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 6)                                                                        Preparation                                                                            2-(2', 3'-dimethyl-                                                                     α-chloro, α-methyl                                                          0.82                                                                              12  Color-                                                                             58.0                                                                              7.2                                                                              19.6                         Example 7                                                                              phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (58.4)                                                                            (6.9)                                                                            (20.0)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 7)                                                                        Preparation                                                                            2-(2',3'-dimethyl-                                                                      α-fluoro-propionic                                                                0.48                                                                              8   Color-                                                                             60.0                                                                              6.9                                                                              22.3                         Example 8                                                                              phenoxy)-1-methyl-                                                                      acid n-butyl ester                                                                              less,                                                                              (60.2)                                                                            (6.9)                                                                            (21.9)                       (Compound                                                                              ethyl biganide              resinous                                 No. 8)                                                                        Preparation                                                                            2-(3',5'-dimethyl-                                                                      α-chloro, α-methyl                                                          2.01                                                                              29  Color-                                                                             57.9                                                                              7.0                                                                              20.2                         Example 9                                                                              phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (58.4)                                                                            (6.9)                                                                            (20.0)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 9)                                                                        Preparation                                                                            2-(3',5'-dimethyl-                                                                      α-bromo, α-methyl                                                           1.85                                                                              24  Color-                                                                             52.2                                                                              6.0                                                                              17.5                         Example 10                                                                             phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (51.8)                                                                            (6.1)                                                                            (17.8)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 10)                                                                       Preparation                                                                            2-(3'-trifluoro-                                                                        α-fluoro, α-methyl                                                          2.09                                                                              28  Color-                                                                             51.9                                                                              5.0                                                                              18.4                         Example 11                                                                             methylphenoxy)-1-                                                                       propionic acid    less,                                                                              (51.5)                                                                            (5.1)                                                                            (18.8)                       (Compound                                                                              methyl-ethyl                                                                            ethyl ester       resinous                                 No. 11)  biganide                                                             Preparation                                                                            2-(3'-methyl-                                                                           α-fluoro, α-methyl                                                          1.32                                                                              21  95.3-                                                                              60.0                                                                              6.8                                                                              22.2                         Example 12                                                                             phenoxy)-1-methyl                                                                       propionic acid    97.0 (60.2)                                                                            (6.9)                                                                            (21.9)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester                                                No. 12)                                                                       Preparation                                                                            2-(3'-methyl-                                                                           α-fluoro-propionic                                                                0.45                                                                              7   Color-                                                                             59.2                                                                              6.9                                                                              22.5                         Example 13                                                                             phenoxy)-1-methyl                                                                       acid n-butyl ester                                                                              less,                                                                              (59.0)                                                                            (6.6)                                                                            (22.9)                       (Compound                                                                              ethyl biganide              resinous                                 No. 13)                                                                       Preparation                                                                            2-(3'-trifluoro-                                                                        α-fluoro-propionic                                                                1.09                                                                              15  Color-                                                                             50.5                                                                              4.5                                                                              19.9                         Example 14                                                                             methylphenoxy)-1-                                                                       acid n-butyl ester                                                                              less,                                                                              (50.1)                                                                            (4.8)                                                                            (19.5)                       (Compound                                                                              methyl-ethyl                resinous                                 No. 14)  biganide                                                             Preparation                                                                            2-(3'-methyl-                                                                           α-chloro, α-methyl                                                          1.11                                                                              16  Color-                                                                             57.0                                                                              6.9                                                                              20.5                         Example 15                                                                             phenoxy)-1-methyl                                                                       propionic acid    less,                                                                              (57.2)                                                                            (6.6)                                                                            (20.9)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 15)                                                                       Preparation                                                                            2-phenoxy α-chloro, α-methyl                                                          1.04                                                                              16  Color-                                                                             56.4                                                                              6.1                                                                              22.0                         Example 16                                                                             1-methyl-ethyl                                                                          propionic acid    less,                                                                              (56.0)                                                                            (6.3)                                                                            (21.8)                       (Compound                                                                              biganide  ethyl ester       resinous                                 No. 16)                                                                       Preparation                                                                            2-phenoxy α-fluoro, α-methyl                                                          1.64                                                                              27  Color-                                                                             58.7                                                                              6.8                                                                              23.1                         Example 17                                                                             1-methyl-ethyl                                                                          propionic acid    less,                                                                              (59.0)                                                                            (6.6)                                                                            (22.9)                       (Compound                                                                              biganide  ethyl ester       resinous                                 No. 17)                                                                       Preparation                                                                            2-phenoxy α-fluoro-propionic                                                                0.58                                                                              9.6 Color-                                                                             58.1                                                                              6.0                                                                              24.2                         Example 18                                                                             1-methyl-ethyl                                                                          acid n-butyl ester                                                                              less,                                                                              (57.7)                                                                            (6.1)                                                                            (24.0)                       (Compound                                                                              biganide                    resinous                                 No. 18)                                                                       Preparation                                                                            2-(3'-methoxy-                                                                          α-fluoro, α-methyl                                                          1.42                                                                              21  Color-                                                                             56.9                                                                              6.8                                                                              20.7                         Example 19                                                                             phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (57.3)                                                                            (6.6)                                                                            (20.9)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 19)                                                                       Preparation                                                                            2-(3',4'-dimethyl-                                                                      α-fluoro, α-methyl                                                          0.61                                                                              9.2 Color-                                                                             60.8                                                                              6.9                                                                              21.3                         Example 20                                                                             phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (61.2)                                                                            (7.3)                                                                            (21.0)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 20)                                                                       Preparation                                                                            2-(3'-fluoro-                                                                           α-fluoro, α-methyl                                                          3.88                                                                              60  Color-                                                                             55.9                                                                              5.6                                                                              22.0                         Example 21                                                                             phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (55.7)                                                                            (5.9)                                                                            (21.7)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 21)                                                                       Preparation                                                                            2-(2'-fluoro-                                                                           α-fluoro, α-methyl                                                          0.19                                                                              3   Color-                                                                             56.0                                                                              6.2                                                                              21.5                         Example 22                                                                             phenoxy)-1-methyl                                                                       propionic acid    less,                                                                              (55.7)                                                                            (5.9)                                                                            (21.7)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 22)                                                                       Preparation                                                                            2-(4'-fluoro-                                                                           α-fluoro, α-methyl                                                          0.84                                                                              13  Color-                                                                             55.2                                                                              5.8                                                                              21.6                         Example 23                                                                             phenoxy)-1-methyl-                                                                      propionic acid    less,                                                                              (55.7)                                                                            (5.9)                                                                            (21.7)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester       resinous                                 No. 23)                                                                       Preparation                                                                            1-(benzofuran-                                                                          α-fluoro, α-methyl                                                          4.74                                                                              75  161.5-                                                                             60.7                                                                              5.9                                                                              22.5                         Example 24                                                                             2'-yl) ethyl                                                                            propionic acid    162.4                                                                              (60.9)                                                                            (5.8)                                                                            (22.2)                       (Compound                                                                              biganide  ethyl ester                                                No. 24)                                                                       Preparation                                                                            1-(benzofuran-                                                                          α-chloro, α-methyl                                                          5.64                                                                              85  138.8-                                                                             57.5                                                                              5.2                                                                              20.8                         Example 25                                                                             2'-yl) ethyl                                                                            propionic acid    139.7                                                                              (57.9)                                                                            (5.5)                                                                            (21.1)                       (Compound                                                                              biganide  methyl ester                                               No. 25)                                                                       Preparation                                                                            1-(benzofuran-                                                                          α-bromo, α-methyl                                                           5.56                                                                              74  149.8-                                                                             51.3                                                                              4.6                                                                              18.3                         Example 26                                                                             2'-yl) ethyl                                                                            propionic acid    150.7                                                                              (51.1)                                                                            (4.8)                                                                            (18.6)                       (Compound                                                                              biganide  ethyl ester                                                No. 26)                                                                       Preparation                                                                            1-(benzofuran-                                                                          α-fluoro-propionic                                                                2.84                                                                              47  139.0-                                                                             59.6                                                                              5.1                                                                              23.5                         Example 27                                                                             2'-yl) ethyl                                                                            acid ethyl ester  140.2                                                                              (59.8)                                                                            (5.4)                                                                            (23.2)                       (Compound                                                                              biganide                                                             No. 27)                                                                       Preparation                                                                            1-(benzofuran-                                                                          α-chloro-propionic                                                                5.02                                                                              79  145.3-                                                                             56.5                                                                              5.3                                                                              22.3                         Example 28                                                                             2'-yl) ethyl                                                                            acid methyl ester 147.4                                                                              (56.7)                                                                            (5.1)                                                                            (22.0)                       (Compound                                                                              biganide                                                             No. 28)                                                                       Preparation                                                                            1-(benzofuran-                                                                          α-fluoro-α-methyl                                                           3.20                                                                              48  153.9-                                                                             62.2                                                                              6.4                                                                              21.1                         Example 29                                                                             2' -yl) ethyl                                                                           butyric acid      155.2                                                                              (62.0)                                                                            (6.1)                                                                            (21.3)                       (Compound                                                                              biganide  methyl ester                                               No. 29)                                                                       Preparation                                                                            1-(benzothiophen                                                                        α-fluoro, α-methyl                                                          4.76                                                                              72  134.2-                                                                             58.2                                                                              5.3                                                                              20.9                         Example 30                                                                             2'-yl) ethyl                                                                            propionic acid    136.0                                                                              (58.0)                                                                            (5.5)                                                                            (21.1)                       (Compound                                                                              biganide  ethyl ester                                                No. 30)                                                                       Preparation                                                                            1-(benzothiophen                                                                        α-chloro, α-methyl                                                          4.86                                                                              70  Color-                                                                             55.0                                                                              5.4                                                                              20.3                         Example 31                                                                             2'-yl) ethyl                                                                            propionic acid    less,                                                                              (55.2)                                                                            (5.2)                                                                            (20.1)                       (Compound                                                                              biganide  methyl ester      resinous                                 No. 31)                                                                       Preparation                                                                            1-(benzothiophen                                                                        α-fluoro-propionic                                                                2.28                                                                              36  Color-                                                                             57.0                                                                              4.9                                                                              22.5                         Example 32                                                                             2'-yl) ethyl                                                                            acid ethyl ester  less,                                                                              (56.8)                                                                            (5.1)                                                                            (22.1)                       (Compound                                                                              biganide                    resinous                                 No. 32)                                                                       Preparation                                                                            1-(6'-methyl-                                                                           α-fluoro, α-methyl                                                          5.54                                                                              84  168.5-                                                                             62.4                                                                              6.0                                                                              21.1                         Example 33                                                                             benzofuran-2'-yl)                                                                       propionic acid    169.3                                                                              (62.0)                                                                            (6.1)                                                                            (21.3)                       (Compound                                                                              ethyl biganide                                                                          ethyl ester                                                No. 33)  hydrochloride                                                        Preparation                                                                            1-(6'-methyl-                                                                           α-fluoro-propionic                                                                3.28                                                                              52  Color-                                                                             61.2                                                                              5.6                                                                              22.0                         Example 34                                                                             benzofuran-2'-yl)                                                                       acid ethyl ester  less (60.9)                                                                            (5.8)                                                                            (22.2)                       (Compound                                                                              ethyl biganide              resinous                                 No. 34)  hydrochloride                                                        Preparation                                                                            1-(6'-methyl-                                                                           α-chloro, α-methyl                                                          5.18                                                                              75  Color-                                                                             58.7                                                                              5.8                                                                              20.4                         Example 35                                                                             benzofuran-2'-yl)                                                                       propionic acid    less,                                                                              (59.0)                                                                            (5.8)                                                                            (20.3)                       (Compound                                                                              ethyl biganide                                                                          methyl ester      resinous                                 No. 35)  hydrochloride                                                        Preparation                                                                            2-(3'-methoxy, 4'-                                                                      α-fluoro, α-methyl                                                          2.17                                                                              34  115.1-                                                                             58.7                                                                              6.7                                                                              21.6                         Example 36                                                                             methylphenyl)-1-                                                                        propionic acid    116.8                                                                              (60.2)                                                                            (6.9)                                                                            (21.9)                       (Compound                                                                              methyl-ethyl                                                                            ethyl ester                                                No. 36)  biganide                                                                      hydrochloride                                                        Preparation                                                                            2-(3'-methoxy, 4'-                                                                      α-fluoro-propionic                                                                1.34                                                                              22  Color-                                                                             57.3                                                                              6.5                                                                              22.8                         Example 37                                                                             methylphenyl)-1-                                                                        acid n-butyl ester                                                                              less,                                                                              (59.0)                                                                            (6.6)                                                                            (22.9)                       (Compound                                                                              methyl-ethyl                resinous                                 No. 37)  biganide                                                                      hydrochloride                                                        Preparation                                                                            2-(3'-methoxy, 4'-                                                                      α-chloro, α-methyl                                                          2.42                                                                              36  Color-                                                                             57.4                                                                              6.7                                                                              20.6                         Example 38                                                                             methylphenyl)-1-                                                                        propionic acid    less,                                                                              (57.2)                                                                            (6.6)                                                                            (20.9)                       (Compound                                                                              methyl-ethyl                                                                            ethyl ester       resinous                                 No. 38)  biganide                                                                      hydrochloride                                                        Preparation                                                                            2-(3'-methyl, 4'-                                                                       α-fluoro, α-methyl                                                          1.98                                                                              31  Color-                                                                             60.3                                                                              6.8                                                                              22.2                         Example 39                                                                             methoxyphenyl)-1-                                                                       propionic acid    less (60.2)                                                                            (6.9)                                                                            (21.9)                       (Compound                                                                              methyl-ethyl                                                                            ethyl ester       resinous                                 No. 39)  biganide                                                                      hydrochloride                                                        Preparation                                                                            2-(3'-methyl, 4'-                                                                       α-fluoro-propionic                                                                1.22                                                                              20  Color-                                                                             59.1                                                                              6.9                                                                              22.7                         Example 40                                                                             methoxyphenyl)-1-                                                                       acid n-butyl ester                                                                              less,                                                                              (59.0)                                                                            (6.6)                                                                            (22.9)                       (Compound                                                                              methyl-ethyl                resinous                                 No. 40)  biganide                                                                      hydrochloride                                                        Preparation                                                                            2-(3'-methyl, 4'-                                                                       α-chloro, α-methyl                                                          2.22                                                                              33  Color-                                                                             57.0                                                                              6.8                                                                              21.0                         Example 41                                                                             methoxyphenyl)-1-                                                                       propionic acid    less,                                                                              (57.2)                                                                            (6.6)                                                                            (20.9)                       (Compound                                                                              methyl-ethyl                                                                            ethyl ester       resinous                                 No. 41)  biganide                                                                      hydrochloride                                                        __________________________________________________________________________     *The value in the brackets show the theoretical value.                   

                                      TABLE 2                                     __________________________________________________________________________                                        Molecular weight                                                              of triazine                               No.    Structural formula of triazine derivative                                                                  derivative                                                                              Triazine derivative             __________________________________________________________________________    Preparation Example 1                                                                 ##STR19##                   C.sub.17 H.sub.24 N.sub.5 OF 333.4                                                      2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  3',5'-dimethyl- phenoxy)-1-m                                                  ethyl-ethylamino]- s-triazin                                                  e                               Preparation Example 2                                                                 ##STR20##                   C.sub.16 H.sub.22 N.sub.5 OF 319.4                                                      2-amino-4-(α-fluoroeth                                                  yl)-6- [2-(3',5'-dimethylphe                                                  noxy)- 1-methyl-ethylamino]-                                                  s-triazine                      Preparation Example 3                                                                 ##STR21##                   C.sub.16 H.sub.22 N.sub.5 OCl                                                           2-amino-4-(α-chloroeth                                                  yl)-6- [2-(3',5'-dimethylphe                                                  noxy)-1- methyl-ethylamino]-                                                  s-triazine                      Preparation Example 4                                                                 ##STR22##                   C.sub.17 H.sub.24 N.sub.5 OF 333.4                                                      2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  2',3'-dimethyl- phenoxy)-1-m                                                  ethyl-ethylamino]- s-triazin                                                  e                               Preparation Example 5                                                                 ##STR23##                   C.sub.17 H.sub.24 N.sub.5 OF 333.4                                                      2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  2',5'-dimethyl- phenoxy)-1-m                                                  ethyl-ethylamino]- s-triazin                                                  e                               Preparation Example 6                                                                 ##STR24##                   C.sub.17 H.sub.24 N.sub.5 OCl                                                           2-amino-4-(α-chloro,                                                    α-methyl ethyl)-6-[2-(                                                  2',5'-dimethyl- phenoxy)-1-m                                                  ethyl-ethylamino]- s-triazin                                                  e                               Preparation Example 7                                                                 ##STR25##                   C.sub.17 H.sub.24 N.sub.5 OCl                                                           2-amino-4-(α-chloro,                                                    α-methyl ethyl)-6-[2-(                                                  2',3'-dimethyl- phenoxy)-1-m                                                  ethyl-ethylamino]- s-triazin                                                  e                               Preparation Example 8                                                                 ##STR26##                   C.sub.16 H.sub.22 N.sub.5 OF 319.4                                                      2-amino-4-(α-fluoroeth                                                  yl)-6- [2-(2',3'-dimethylphe                                                  noxy)- 1-methyl-ethylamino]-                                                  s-triazine                      Preparation Example 9                                                                 ##STR27##                   C.sub.17 H.sub.24 N.sub.5 OCl                                                           2-amino-4-(α-chloro,                                                    α-methyl ethyl)-6-[2-(                                                  3',5'-dimethyl- phenoxy)-1-m                                                  ethyl-ethylamino]- s-triazin                                                  e                               Preparation Example 10                                                                ##STR28##                   C.sub.17 H.sub.24 N.sub.5 OBr                                                           2-amino-4-(α-bromo,                                                     α-methyl ethyl)-6-[2-(                                                  3',5'-dimethyl- phenoxy)-1-m                                                  ethyl-ethylamino]- s-triazin                                                  e                               Preparation Example 11                                                                ##STR29##                   C.sub.16 H.sub.19 N.sub.5 OF.sub.4                                            373.4     2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  3'-trifluoro- methylphenoxy)                                                  -1-methyl-ethyl- amino]-s-tr                                                  iazine                          Preparation Example 12                                                                ##STR30##                   C.sub.16 H.sub.22 N.sub.5                                                               2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  3'-methylphenoxy)-1-                                                          methyl-ethylamino]-s-triazin                                                  e                               Preparation Example 13                                                                ##STR31##                   C.sub.15 H.sub.20 N.sub.5 OF 305.4                                                      2-amino-4-(α-fluoroeth                                                  yl)-6- [2-(3'-methylphenoxy)                                                  -1- methyl-ethylamino]-s-tri                                                  azine                           Preparation Example 14                                                                ##STR32##                   C.sub.15 H.sub.17 N.sub.5 OF.sub.4                                            359.3     2-amino-4-(α-fluoroeth                                                  yl)-6- [2-(3'-trifluoromethy                                                  lphenoxy)- 1-methyl-ethylami                                                  no]-s-triazine                  Preparation Example 15                                                                ##STR33##                   C.sub.16 H.sub.22 N.sub.5 OCl                                                           2-amino-4-(α-chloro,                                                    α-methyl ethyl)-6-[2-(                                                  3'-methylphenoxy)- 1-methyl-                                                  ethylamino]-s-triazine          Preparation Example 16                                                                ##STR34##                   C.sub.15 H.sub.20 N.sub.5 OCl                                                           2-amino-4-(α-chloro,                                                    α-methyl ethyl)-6-(2-p                                                  henoxy)-1-methyl- ethylamino                                                  )-s-triazine                    Preparation Example 17                                                                ##STR35##                   C.sub.15 H.sub.20 N.sub.5 OF 305.4                                                      2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-(2-p                                                  henoxy)-1-methyl- ethylamino                                                  )-s-triazine                    Preparation Example 18                                                                ##STR36##                   C.sub.14 H.sub.18 N.sub.5 OF 291.3                                                      2-amino-4-(α-fluoroeth                                                  yl)-6- (2-phenoxy-1-methyl-e                                                  thylamino)- s-triazine          Preparation Example 19                                                                ##STR37##                   C.sub.16 H.sub.22 N.sub.5 O.sub.2 F                                           335.4     2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  3'-methoxyphenoxy)-                                                           1-methyl-ethylamino]-s-triaz                                                  ine                             Preparation Example 20                                                                ##STR38##                   C.sub.17 H.sub.24 N.sub.5 OF 333.4                                                      2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  3',4'-dimethyl- phenoxy)-1-m                                                  ethyl-ethylamino]- s-triazin                                                  e                               Preparation Example 21                                                                ##STR39##                   C.sub.15 H.sub.19 N.sub.5 OF.sub.2                                            323.3     2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  3'-fluorophenoxy)- 1-methyl-                                                  ethylamino]-s-triazine          Preparation Example 22                                                                ##STR40##                   C.sub.15 H.sub.19 N.sub.5 OF.sub.2                                            323.3     2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  2'-fluorophenoxy)- 1-methyl-                                                  ethylamino]-s-triazine          Preparation Example 23                                                                ##STR41##                   C.sub.15 H.sub.19 N.sub. 5 OF.sub.2                                           323.3     2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  4'-fluorophenoxy)- 1-methyl-                                                  ethylamino]-s-triazine          Preparation Example 24                                                                ##STR42##                   C.sub.16 H.sub.18 N.sub.5 OF 315.4                                                      2-amino-4-[1-(benzofuran-2'-                                                   yl)ethylamino]-6-(α-f                                                  luoro, α- methyl                                                        ethyl)-s-triazine               Preparation Example 25                                                                ##STR43##                   C.sub.16 H.sub.18 N.sub.5 OCl                                                           2-amino-4-[1-(benzofuran-2'-                                                   yl)ethylamino]                                                               -6-(α-chloro,                                                           α- methyl                                                               ethyl)-s-triazine               Preparation Example 26                                                                ##STR44##                   C.sub.16 H.sub.18 N.sub.5 OBr                                                           2-amino-4-[1-(benzofuran-2'-                                                   yl)ethylamino]-6-(α-b                                                  romo, α- methyl                                                         ethyl)-s-triazine               Preparation Example 27                                                                ##STR45##                   C.sub.15 H.sub.16 N.sub.5 OF 301.3                                                      2-amino-4-[1-(benzofuran-2'-                                                   yl)ethylamino]-6-(α-f                                                  luoroethyl)- s-triazine         Preparation Example 28                                                                ##STR46##                   C.sub.15 H.sub.16 N.sub.5 OCl                                                           2-amino-4-[1-(benzofuran-2'-                                                   yl)ethylamino]-6-(α-c                                                  hloroethyl)- s-triazine         Preparation Example 29                                                                ##STR47##                   C.sub.17 H.sub.20 N.sub.5 OF 329.4                                                      2-amino-4-[1-(benzofuran-2'-                                                   yl)ethylamino]-6-(α-f                                                  luoro, α- methyl                                                        propyl)-s-triazine              Preparation Example 30                                                                ##STR48##                   C.sub.16 H.sub.18 N.sub.5 SF 331.4                                                      2-amino-4-[1-(benzothiophen-                                                   2'-yl)ethylamino]-6-(.alpha                                                  .-fluoro, α-methyl                                                      propyl)-s-triazine              Preparation Example 31                                                                ##STR49##                   C.sub.16 H.sub.18 N.sub.5 SCl                                                           2-amino-4-[1-(benzothiophen-                                                  2'- yl)ethylamino]-6-(.alpha                                                  .-chloro, α- methyl                                                     ethyl)-s-triazine               Preparation Example 32                                                                ##STR50##                   C.sub.15 H.sub.16 N.sub.5 SF 317.4                                                      2-amino-4-[1-(benzothiophen-                                                  2'- yl)ethylamino]-6-(.alpha                                                  .-fluoroethyl)- s-triazine      Preparation Example 33                                                                ##STR51##                   C.sub.17 H.sub.20 N.sub.5 OF 329.4                                                      2-amino-4-[1-(6'-methylbenzo                                                  - furan-2'-yl)ethylamino]-6-                                                   (α-fluoro,                                                             α-methyl ethyl)-s-                                                      triazine                        Preparation Example 34                                                                ##STR52##                   C.sub.16 H.sub.18 N.sub.5 OF 315.4                                                      2-amino-4-[1-(6'-methylbenzo                                                  furan- 2'-yl)ethylamino]-6-(                                                  α-fluoro- ethyl)-s-tri                                                  azine                           Preparation Example 35                                                                ##STR53##                   C.sub.17 H.sub.20 N.sub.5 OCl                                                           2-amino-4-[1-6'-methylbenzof                                                  uran- 2'-yl)ethylamino]-6-(.                                                  alpha.-chloro, α-methy                                                  l ethyl)-s-triazine             Preparation Example 36                                                                ##STR54##                   C.sub.18 H.sub.22 N.sub.5 OF 319.4                                                      2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  3'-methyloxy,                                                                 4'- methylphenyl)-1-methyl-                                                   thylamino]-s-triazine           Preparation Example 37                                                                ##STR55##                   C.sub.15 H.sub.20 N.sub.5 OF 305.4                                                      2-amino-4-(α-fluoroeth                                                  yl)-6- [2-(3'-methoxy,                                                        4'-methylphenyl)- 1-methyl-e                                                  thylamino]-s-triazine           Preparation Example 38                                                                ##STR56##                   C.sub.18 H.sub.22 N.sub.5 OCl                                                           2-amino-4-(α-chloro,                                                    α-methyl)- 6-[2-(3'-me                                                  thoxy, 4'-methylphenyl)-                                                      1-methyl-ethylamino]-s-triaz                                                  ine                             Preparation Example 39                                                                ##STR57##                   C.sub.16 H.sub.22 N.sub.5 OF 319.4                                                      2-amino-4-(α-fluoro,                                                    α-methyl ethyl)-6-[2-(                                                  3'-methyl,                                                                    4'- methoxyphenyl)-1-methyl-                                                   ethylamino]-s-triazine         Preparation Example 40                                                                ##STR58##                   C.sub.15 H.sub.20 N.sub.5 OF 305.4                                                      2-amino-4-(α-fluoroeth                                                  yl-6- [2-(3'-methyl,                                                          4'-methoxyphenyl)- 1-methyl-                                                  ethylamino]-s-triazine          Preparation Example 41                                                                ##STR59##                   C.sub.16 H.sub.22 N.sub.5 OCl                                                           2-amino-4-(α-fluoro,                                                    α-methylethyl)-                                                         6-[2-(3'-methyl,                                                              4'-methoxyphenyl)- 1-methyl-                                                  ethylamino]-s-triazine          __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________    Preparation                                                                          Compound                                                                             Infrared absorption*.sup.1                                      Example No.                                                                          prepared                                                                             spectrum (cm.sup.-1)                                                                     Proton nuclear magnetic resonance                                             spectrum*.sup.2 (ppm)                                __________________________________________________________________________     1     Compound 1                                                                           3470, 3350, 3280                                                                         1.35(3H, d), 1.65(6H, d), 2.28(6H, s),                                        3.91˜3.99(2H, m),                                            1660, 1620, 1560                                                                         4.25˜4.70(1H, brs), 5.44˜5.80(3H,                                 brs), 6.55˜6.60(3H, m)                                                  solvent: deuterated chloroform                        2     Compound 2                                                                           3500, 3440, 3200                                                                         1.33(3H, d), 1.60(3H, q), 2.26(6H, s),                                        3.90˜4.03(2H, m),                                            1660, 1620, 1560                                                                         4.30˜4.63(1H, brs), 4.80˜5.14(1H,                                 m), 5.38˜5.77(3H, m),                                                   6.52˜6.60(3H, m) solvent: deuterated                                    chloroform                                            3     Compound 3                                                                           3500, 3420, 3330                                                                         1.32(3H, d), 1.70(3H, d), 2.23(6H, s),                                        3.80˜4.18(2H, m),                                            1660, 1620, 1560                                                                         4.32˜4.80(3H, m), 6.50˜6.60(4H, brs)                              solvent: deuterated                                                           acetone                                               4     Compound 4                                                                           3510, 3350, 3200                                                                         1.38(3H, d), 1.55(3H, d), 2.10(3H, s), 2.23(3H,                               s), 3.80˜                                                    1660, 1620, 1560                                                                         4.21(2H, m), 4.30˜4.78(2H, brs),                                        6.18˜7.42(6H, brs)                                                      solvent: deuterated acetone                           5     Compound 5                                                                           3470, 3350, 3250                                                                         1.37(3H, d), 1.63(6H, d), 2.17(3H, s), 2.30(3H,                               s), 3.96˜                                                    1658, 1586, 1540                                                                         4.00(2H, m), 4.32˜4.78(1H, brs),                                        5.26˜5.73(3H, brs),                                                     6.62˜7.35(3H, m) solvent: deuterated                                    chloroform                                            6     Compound 6                                                                           3530, 3360, 3250                                                                         1.40(3H, d), 1.88(6H, s), 2.19(3H, s), 2.31(3H,                               s), 3.96˜                                                    1650, 1580, 1575                                                                         4.03(2H, m), 4.32˜4.80(1H, brs),                                        5.32˜5.92(3H, brs),                                                     6.54˜7.22(3H, m) solvent: deuterated                                    chloroform                                            7     Compound 7                                                                           3500, 3350, 3200                                                                         1.39(3H, d), 1.88(6H, s), 2.16(3H, s), 2.27(3H,                               s), 3.91˜                                                    1650, 1590, 1560                                                                         4.01(2H, m), 4.28˜4.82(1H, brs),                                        5.28˜5.88(3H, brs),                                                     6.64˜7.29(3H, m) solvent: deuterated                                    chloroform                                            8     Compound 8                                                                           3530, 3360, 3220                                                                         1.38(3H, d), 1.62(3H, q), 2.14(3H, s), 2.28(3H,                               s), 3.95˜                                                    1660, 1580, 1560                                                                         4.00(2H, m), 4.32˜4.75(1H, brs),                                        4.87˜5.57(4H, brs),                                                     6.64˜7.20(3H, m) solvent: deuterated                                    chloroform                                            9     Compound 9                                                                           3460, 3350, 3200                                                                         1.35(3H, d), 1.89(6H, s), 2.30(6H, s),                                        3.88˜4.05(2H, m),                                            1660, 1620, 1550                                                                         4.24˜4.72(1H, brs), 5.16˜5.77(3H,                                 brs), 6.42˜6.79(3H, m)                                                  solvent: deuterated chloroform                       10     Compound 10                                                                          3500, 3360, 3200                                                                         1.37(3H, d), 2.08(6H, s), 2.29(6H, s),                                        3.84˜4.07(2H, m),                                            1640, 1600, 1560                                                                         4.26˜4.77(1H, brs), 5.08˜5.77(3H,                                 brs), 6.44˜6.75(3H, m)                                                  solvent: deuterated chloroform                       11     Compound 11                                                                          3530, 3360, 3200                                                                         1.37(3H, d), 1.63(6H, d), 3.93˜4.09(2H,                                 m), 4.27˜4.72                                                1600, 1580, 1560                                                                         (1H, brs), 5.52˜6.60(3H, brs),                                          7.02˜7.48(4H, m)                                                        solvent: deuterated chloroform                       12     Compound 12                                                                          3440, 3330 1.36(3H, d), 1.64(6H, d), 2.32(3H, s),                                        3.94˜4.01(2H, m),                                            1650, 1610, 1570                                                                         4.29˜4.65(1H, brs), 5.28˜5.90(3H,                                 brs), 6.74˜7.17(4H, m)                                                  solvent: deuterated chloroform                       13     Compound 13                                                                          3500, 3340, 3190                                                                         1.36(3H, d), 1.62(3H, q), 2.32(3H, s),                                        3.94˜4.00(2H, m),                                            1640, 1620, 1564                                                                         4.19˜4.70(1H, brs), 4.96(1H, q),                                        5.17˜5.99(3H, brs),                                                     6.68˜7.24(4H, m) solvent: deuterated                                    chloroform                                           14     Compound 14                                                                          3500, 3350, 3200                                                                         1.36(3H, d), 1.62(3H, q), 3.98˜4.08(2H,                                 m), 4.29˜4.70                                                1640, 1600, 1560                                                                         (1H, brs), 4.97(1H, q), 5.39˜6.50(3H,                                   brs)                                                                          solvent: deuterated chloroform                       15     Compound 15                                                                          3500, 3350, 3230                                                                         1.35(3H, d), 1.88(6H, s), 2.32(3H, s),                                        3.94˜4.01(2H, m),                                            1655, 1600, 1575                                                                         4.23˜4.77(1H, brs), 5.09˜5.99(3H,                                 brs), 6.68˜7.16(4H, m)                                                  solvent: deuterated chloroform                       16     Compound 16                                                                          3500, 3360, 3220                                                                         1.33(3H, d), 1.89(6H, s), 3.97˜4.04(2H,                                 m), 4.26˜4.76                                                1655, 1600, 1460                                                                         (1H, brs), 4.96˜ 5.73(3H, brs),                                         6.87˜7.38(5H, m)                                                        solvent: deuterated chloroform                       17     Compound 17                                                                          3500, 3380, 3180                                                                         1.34(3H, d), 1.63(6H, d), 3.93˜4.01(2H,                                 m), 4.18˜4.70                                                1650, 1600, 1560                                                                         (1H, brs), 5.61˜5.58(3H, brs),                                          6.84˜7.38(5H, m)                                                        solvent: deuterated chloroform                       18     Compound 18                                                                          3510, 3350, 3200                                                                         1.34(3H, d), 1.60(3H, q), 3.88˜4.00(2H,                                 m), 4.25˜4.73                                                1660, 1610, 1560                                                                         (1H, brs), 4.95(1H, q), 5.38˜6.62(3H,                                   brs), 6.83˜7.36                                                         (5H, m) solvent: deuterated chloroform               19     Compound 19                                                                          3470, 3380, 3220                                                                         1.36(3H, d), 1.64(6H, d), 3.79(3H, s),                                        3.91˜4.04(2H, m),                                            1650, 1610, 1575                                                                         4.28˜4.65(1H, brs), 5.32˜5.92(3H,                                 brs), 6.48˜7.17(4H, m)                                                  solvent: deuterated chloroform                       20     Compound 20                                                                          3440, 3330, 3200                                                                         1.33(3H, d), 1.62(6H, d), 2.17(3H, s), 2.21(3H,                               s), 3.89˜                                                    1650, 1595, 1560                                                                         3.96(2H, m), 4.20˜4.67(1H, brs),                                        5.48˜6.48(3H, brs),                                                     6.57˜7.12(3H, m) solvent: deuterated                                    chloroform                                           21     Compound 20                                                                          3440, 3330, 3240                                                                         1.35(3H, d), 1.64(6H, d), 3.93˜4.03(2H,                                 m), 4.26˜4.67                                                1640, 1585, 1560                                                                         (1H, brs), 5.22˜5.92(3H, brs),                                          6.59˜7.37(4H, m)                                                        solvent: deuterated chloroform                       22     Compound 22                                                                          3500, 3320, 3240                                                                         1.39(3H, d), 1.64(6H, d), 4.01˜ 4.10(2H,                                m), 4.29˜4.72                                                1650, 1600, 1570                                                                         (1H, brs), 5.07˜5.74(3H, brs),                                          6.99˜7.02(4H, m)                                                        solvent: deuterated chloroform                       23     Compound 23                                                                          3520, 3350, 3220                                                                         1.36(3H, d), 1.64(6H, d), 3.91˜3.99(2H,                                 m), 4.23˜4.74                                                1660, 1600, 1560                                                                         (1H, brs), 5.13˜5.68(3H, brs),                                          6.86˜6.98(4H, m)                                                        solvent: deuterated chloroform                       24     Compound 24                                                                          3500, 3310, 3220                                                                         1.56(6H, d), 1.65(3H, d), 5.30˜5.71(1H,                                 m), 6.20˜6.59                                                1660, 1600, 1540                                                                         (2H, brs), 6.69(1H, s), 7.12˜7.64(4H, m)                                solvent: deuterated                                                           acetone                                              25     Compound 25                                                                          3490, 3340, 3270                                                                         1.62(3H, d), 1.89(6H, s), 5.25˜5.78(1H,                                 m), 6.57(1H, s),                                                   1640, 1610, 1560                                                                         7.11˜7.56(4H, m) solvent: deuterated                                    acetone                                              26     Compound 26                                                                          3490, 3350 1.63(3H, d), 2.07(6H, s), 5.24˜5.77(1H,                                 m), 6.57(1H, s),                                                   1650, 1580, 1560                                                                         7.16˜7.58(4H, m) solvent: deuterated                                    acetone                                              27     Compound 27                                                                          3490, 3320, 3190                                                                         1.60(3H, d, d), 1.61(3H, d), 4.90˜5.42(1H,                              q, q), 5.40˜6.08                                             1650, 1600, 1540                                                                         (1H, brs), 6.69(1H, s), 7.11˜7.56(4H, m)                                solvent: deuterated                                                           acetone                                              28     Compound 28                                                                          3490, 3320, 3220                                                                         1.57(3H, d), 1.72(3H, d), 4.69(1H, q),                                        5.24˜5.73(1H, m),                                            1660, 1600, 1560                                                                         6.69(1H, s), 7.08˜7.68(4H, m) solvent:                                  deuterated acetone                                   29     Compound 29                                                                          3460, 3320, 3180                                                                         1.20(3H, t), 1.57(3H, d), 1.65(3H, d), 1.88(1H,                               q), 5.16˜                                                    1650, 1590, 1540                                                                         6.00(4H, brs), 6.57(1H, s), 7.10˜7.56(4H,                               m)                                                                            solvent: deuterated acetone                          30     Compound 30                                                                          3540, 3290, 3150                                                                         1.61(6H, d), 1.62(3H, d), 5.31˜6.42(4H,                                 brs), 7.08˜7.83                                              1660, 1620, 1560                                                                         (5H, m) solvent: deuterated chloroform               31     Compound 31                                                                          3520, 3430, 3360                                                                         1.57(3H, d), 1.87(6H, s), 5.26˜6.33(4H,                                 brs), 6.99˜7.76                                              1650, 1570 (5H, m) solvent: deuterated chloroform               32     Compound 32                                                                          3500, 3430, 3330                                                                         1.53(3H, d, ), 1.62(3H, d), 4.69˜5.88(3H,                               brs), 6.20˜7.19                                              1650, 1570 (3H, brs), 7.21˜7.96(5H, m) solvent:                                    deuterated acetone                                   33     Compound 33                                                                          3510, 3430, 3350                                                                         1.58(6H, d), 1.62(3H, d), 2.41(3H, s),                                        5.22˜5.67(1H, m),                                            1660, 1570 6.28˜6.92(3H, brs), 6.61(1H, s),                                        6.92˜7.49(3H, m)                                                        solvent: deuterated acetone                          34     Compound 34                                                                          3490, 3430, 3330                                                                         1.60(3H, d, d), 1.62(3H, d), 2.42(3H, s),                                     4.72˜5.85(5H, brs),                                          1650, 1570 6.51(1H, s), 6.90˜7.49(3H, m) solvent:                                  deuterated                                                                    chloroform                                           35     Compound 35                                                                          3500, 3430, 3350                                                                         1.62(3H, d), 1.89(6H, s), 2.43(3H, s),                                        5.08˜5.69(4H, brs),                                          1640, 1560 6.52(1H, s), 6.90˜7.49(3H, m) solvent:                                  deuterated                                                                    chloroform                                           36     Compound 36                                                                          3510, 3350, 3210                                                                         1.52(3H, d), 1.55(6H, d), 2.12(3H, s), 3.80(3H,                               s), 5.04˜                                                    1660, 1600, 1570                                                                         5.40(2H, m), 6.48(1H, brs), 6.78˜7.20(3H,                               m)                                                                            solvent: deuterated acetone                          37     Compound 37                                                                          3480, 3400, 3370                                                                         1.50(3H, d), 1.58(3H, d, d), 2.16(3H, s),                                     3.78(3H, s), 5.33˜                                           1670, 1620, 1560                                                                         6.34(4H, m), 6.78˜7.10(3H, m) solvent:                                  deuterated                                                                    chloroform                                           38     Compound 38                                                                          3510, 3440, 3350                                                                         1.52(3H, d), 1.89(6H, s), 3.82(3H, s),                                        4.95˜5.67(4H, brs),                                          1650, 1570 6.76˜7.30(3H, m) solvent: deuterated                                    chloroform                                           39     Compound 39                                                                          3510, 3400, 3320                                                                         1.42(3H, d), 1.60(6H, d), 2.19(3H, s), 3.79(3H,                               s), 4.88˜                                                    1640, 1560 5.29(1H, m), 5.61˜7.20(3H, m) solvent:                                  deuterated                                                                    chloroform                                           40     Compound 40                                                                          3500, 3420, 3330                                                                         1.47(3H, d), 1.56(3H, d, d), 2.19(3H, s),                                     3.79(3H, s), 4.72˜                                           1650, 1570 6.57(5H, brs), 6.64˜7.28(3H, m) solvent:                                deuterated                                                                    chloroform                                           41     Compound 41                                                                          3510, 3420, 3350                                                                         1.51(3H, d), 1.88(6H, s), 2.20(3H, s), 3.81(3H,                               s), 4.85˜                                                    1650, 1630, 1570                                                                         5.58(4H, brs), 6.69˜7.29(3H, m) solvent:                                deuterated                                                                    chloroform                                           __________________________________________________________________________     *.sup.1 KBr tablet method                                                     *.sup.2 Internal standard: tetramethyl silane                            

In the following, the actual method for form preparation is described byway of formulation examples. In the formulation examples given below,"parts" refers to % by weight.

Formulation Example 1 Water-dispersible powder

    ______________________________________                                        Compound of Preparation Example 1                                                                      20    parts                                          Diatomaceous earth       62    parts                                          White carbon             15    parts                                          Sodium alkylbenzene sulfonate                                                                          2     parts                                          Sodium lignin sulfonate  1     part                                           ______________________________________                                    

The above were blended and uniformly mixed and pulverized to give 100parts of a water-dispersible powder.

Formulation Example 2 Emulsion

    ______________________________________                                        Compound of Preparation Example 2                                                                       40 parts                                            Xylene                    20 parts                                            Dimethyl formamide        20 parts                                            Solpol 2806B (surface active agent, manufac-                                                            20 parts                                            tured by Toho Chemical Industry)                                              ______________________________________                                    

The above were uniformly dissolved and mixed to give 100 parts of anemulsion.

Formulation Example 3 Dust

    ______________________________________                                        Compound of Preparation Example 3                                                                     2 parts                                               Diatomaceous earth     20 parts                                               Talc                   78 parts                                               ______________________________________                                    

The above were blended and uniformly mixed and pulverized to give 100parts of a dust.

Formulation Example 4 Granules

    ______________________________________                                        Compound of Preparation Example 4                                                                      1     part                                           Bentonite                30    parts                                          Talc                     66    parts                                          Sodium lignin sulfonate  3     parts                                          ______________________________________                                    

The above were blended, uniformly mixed and pulverized and thoroughlykneaded with addition of water followed by granulation and drying togive 100 parts of granules.

Formulation Example 5 Flowable agent

    ______________________________________                                        Compound of Preparation Example 5                                                                      25     parts                                         Methyl cellulose         0.3    part                                          Colloidal silica         1.5    parts                                         Sodium lignin sulfonate  1      part                                          Polyoxyethylene nonylphenyl ether                                                                      2      parts                                         Water                    70.2   parts                                         ______________________________________                                    

The above were thoroughly mixed and dispersed and the slurry-likemixture was subjected to wet-process pulverization to give 100 parts ofa stable flowable agent.

Formulation Example 6 Water-dispersible Powder

A carrier for water-dispersible powder was obtained by uniformlypulverizing and mixing 97 parts of clay (commercial product name:Zieglite, manufactured by Zieglite Kogyo) as a carrier, 1.5 parts of analkylaryl sulfonic acid salt (commercial product name: Neopelex,manufactured by Kao Atlas Co.) as a surface active agent and 1.5 partsof a non-ionic type and anionic type surface active agent (commercialproduct name: Solpol 800A, manufactured by Toho Chemical Industry Co.).

A water-dispersible powder was obtained by uniformly pulverizing andmixing 90 parts of this carrier for water dispersible powder and 10parts of the triazine derivative obtained in the above describedPreparation Examples 1 to 5.

EXAMPLES 1 to 41 Upland Field Soil Treatment Test

Wagner pots of 1/2000 were filled with a soil of non-paddy field andseeds of Digitaria sanguinalis, Alopecurus myosuroides, Abutilontheophrasti, Veronica persica, Viola arvensis, Polygonum persicaria,Amaranthus patulus, Galium sparium var. echinospermon, wheat, barley,corn and grain sorghum were uniformly sowed in the surface layer.

Prior to the germination of the wheat, barley, corn, grain sorghum andweeds thereafter, the soil surface was uniformly treated with aspecified volume of a diluted solution of the herbicide obtained in theabove described Formulation Example 6 and the pots were kept standing ina greenhouse with periodical water sprinkling.

Table 4 shows the results of the investigations of the herbicidaleffects and phytotoxicity to the wheat, barley, corn and grain sorghumafter 30 days from the treatment with the herbicide solution. The dosewas 25 to 100 g/10 ares calculated as the amount of the effectiveingredient. The phytotoxicity to the wheat, barley, corn and grainsorghum and the herbicidal effects are expressed as shown below bymeasuring the respective air-dried weights.

    ______________________________________                                                        Phytotoxicity to wheat, barley,                                               corn & grain sorgham (relative                                Extent of phytotoxicity                                                                       to untreated zone)                                            ______________________________________                                        0               100%                                                          1               61 to 99%                                                     2               21 to 60%                                                     3               11 to 20%                                                     4                1 to 10%                                                     5                0%                                                           ______________________________________                                    

    ______________________________________                                        Degree of     Herbicidal effects                                              herbicidal effects                                                                          (relative to untreated zone)                                    ______________________________________                                        0             100%                                                            1             61 to 99%                                                       2             21 to 60%                                                       3             11 to 20%                                                       4              1 to 10%                                                       5              0%                                                             ______________________________________                                    

COMPARATIVE EXAMPLES 1 TO 6

The same procedure as in Example 1 was undertaken excepting the use ofthe triazine derivatives A to C (described in the official publicationof Japanese Patent Kokai No. 63-264465), D (described in the officialpublication of Japanese Patent Kokai No. 63-51379), E (described in theofficial publication of Japanese Patent Kokai No. 63-146876) or F(described in the official publication of Japanese Patent Toku-Sai-HyoNo. 88/02368) expressed by the formulas given below in place of thetriazine derivative prepared in Preparation Example 1, in Example 1. Theresults are shown in Table 4. ##STR60##

    TABLE 4      Herbicidal effect    Galium  Amount of  sparium Phytotoxicity  Compound h     erbicide Alopecurus Digitaria Abutilon Veronica Polygonum Viola Amaranthu     s var.    Grain No. used (g/10a) myosuroides sanguinalis theophrasti     persica persicaria arvensis patulus echinospermon Wheat Barley Corn     sorghum       Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 1 Preparation 50 5 5     5 5 5 5 5 5 0 0 0 0  Example 1 25 5 5 5 5 5 5 5 5 0 0 0 0 Example     Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 2 Preparation 50 5 5 5 5 5 5 5     5 0 0 0 0  Example 2 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100     5 5 5 5 5 5 5 5 0 0 0 0 3 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0     Example 3 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5     5 5 5 0 0 0 0 4 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 4 25 5 5     5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 5     Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 5 25 5 5 5 5 5 5 5 5 0 0     0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 6 Preparation 50 5     5 5 5 5 5 5 5 0 0 0 0  Example 6 25 5 5 5 5 5 5 5 5 0 0 0 0 Example     Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 7 Preparation 50 5 5 5 5 5 5 5     5 0 0 0 0  Example 7 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100     5 5 5 5 5 5 5 5 0 0 0 0 8 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0     Example 8 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5     5 5 5 0 0 0 0 9 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 9 25 5 5     5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 10     Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 10 25 5 5 5 5 5 5 5 5 0     0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 11 Preparation 50     5 5 5 5 5 5 5 5 0 0 0 0  Example 11 25 5 5 5 5 5 5 5 5 0 0 0 0 Example     Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 12 Preparation 50 5 5 5 5 5 5 5     5 0 0 0 0  Example 12 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100      5 5 5 5 5 5 5 5 0 0 0 0 13 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0     Example 13 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5     5 5 5 0 0 0 0 14 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 14 25 5     5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0     15 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 15 25 5 5 5 5 5 5 5 5     0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 16 Preparation     50 5 5 5 5 5 5 5 5 0 0 0 0  Example 16 25 5 5 5 5 5 5 5 5 0 0 0 0     Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 17 Preparation 50 5 5 5     5 5 5 5 5 0 0 0 0  Example 17 25 5 5 5 5 5 5 5 0 0 0 0 Example Compound     of 100  5 5 5 5 5 5 5 5 0 0 0 0 18 Preparation 50 5 5 5 5 5 5 5 5 0 0 0     0  Example 18 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5     5 5 5 5 5 0 0 0 0 19 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 19     25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0     0 0 20 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 20 25 5 5 5 5 5 5     5 5 0 0 0 0 Example Compound of 100       5 5 5 5 5 5 5 5 0 0 0 0 21 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0     Example 21 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5     5 5 5 0 0 0 0 22 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 22 25 5     5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0     23 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 23 25 5 5 5 5 5 5 5 5     0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 24 Preparation     50 5 5 5 5 5 5 5 5 0 0 0 0  Example 24 25 5 5 5 5 5 5 5 5 0 0 0 0     Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 25 Preparation 50 5 5 5     5 5 5 5 5 0 0 0 0  Example 25 25 5 5 5 5 5 5 5 5 0 0 0 0 Example     Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 26 Preparation 50 5 5 5 5 5 5 5     5 0 0 0 0  Example 26 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100      5 5 5 5 5 5 5 5 0 0 0 0 27 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0     Example 27 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5     5 5 5 0 0 0 0 28 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 28 25 5     5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0     29 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 29 25 5 5 5 5 5 5 5 5     0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 30 Preparation     50 5 5 5 5 5 5 5 5 0 0 0 0  Example 30 25 5 5 5 5 5 5 5 5 0 0 0 0     Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 31 Preparation 50 5 5 5     5 5 5 5 5 0 0 0 0  Example 31 25 5 5 5 5 5 5 5 5 0 0 0 0 Example     Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 32 Preparation 50 5 5 5 5 5 5 5     5 0 0 0 0  Example 32 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100      5 5 5 5 5 5 5 5 0 0 0 0 33 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0     Example 33 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5     5 5 5 0 0 0 0 34 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 34 25 5     5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0     35 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 35 25 5 5 5 5 5 5 5 5     0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 36 Preparation     50 5 5 5 5 5 5 5 5 0 0 0 0  Example 36 25 5 5 5 5 5 5 5 5 0 0 0 0     Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 37 Preparation 50 5 5 5     5 5 5 5 5 0 0 0 0  Example 37 25 5 5 5 5 5 5 5 5 0 0 0 0 Example     Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0 38 Preparation 50 5 5 5 5 5 5 5     5 0 0 0 0  Example 38 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100      5 5 5 5 5 5 5 5 0 0 0 0 39 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0     Example 39 25 5 5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5     5 5 5 0 0 0 0 40 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 40 25 5     5 5 5 5 5 5 5 0 0 0 0 Example Compound of 100  5 5 5 5 5 5 5 5 0 0 0 0     41 Preparation 50 5 5 5 5 5 5 5 5 0 0 0 0  Example 41 25 5 5 5 5 5 5 5 5     0 0 0 0 Comparative Triazine 100  4 5 4 5 5 4 5 4 0 0 0 0 Example     derivative 50 3 3 4 4 3 3 3 2 0 0 0 0 1 A 25 1 1 2 3 2 2 1 1 0 0 0 0     Comparative Triazine 100  3 3 4 4 3 3 4 2 0 0 0 0 Example derivative 50     1 1 3 3 2 2 3 0 0 0 0 0 2 B 25 0 0 1 1 1 0 1 0 0 0 0 0 Comparative     Triazine 100  5 5 4 5 5 5 5 3 0 0 0 0 Example derivative 50 3 3 4 4 4 4     3 1 0 0 0 0 3 C 25 2 2 3 3 2 2 2 1 0 0 0 0 Comparative Triazine 100  5 5     4 5 5 4 5 4 0 0 0 0 Example derivative 50 3 3 4 4 4 4 4 3 0 0 0 0 4 D 25     3 2 3 3 3 3 3 1 0 0 0 0 Comparative Triazine 100  3 4 4 3 3 4 4 2 0 0 0     0 Example derivative 50 1 2 3 3 3 2 2 0 0 0 0 0 5 E 25 0 0 1 0 0 0 0 0 0     0 0 0 Comparative Triazine 100       3 5 4 5 4 4 5 4 0 0 0 0 Example derivative 50 2 3 3 4 3 4 3 3 0 0 0 0     6 F 25 0 1 2 2 1 2 0 1 0 0 0 0

EXAMPLES 42 TO 82 Foilage Treatment Test

Seeds of weeds including Abutilon theophrasti, Common blackjack,Amaranthus patulus, Cassia obtusifolia, Ipomoea purpurea, Galium spariumvar. echinospermon, Veronica persica and seeds of crops including corn,grain sorghum, wheat, barley and oat were sowed on to the Wagner pots of1/2000 filled with soil of upland field and, after covering up withsoil, were grown in a greenhouse and, when the weeds were in their mono-to bi-foliate period and the crops were in their tri-foliate period, anaqueous suspension of a specified amount of the herbicide prepared inthe above described Formulation Example 6 was uniformly sprinkled byspraying to the parts of stems and leaves in a liquid volumecorresponding to 100 liters/10 ares. Thereafter, they were grown in agreenhouse and the phytotoxicity on the crops and the herbicidal effectswere estimated according to the following criteria on the 20th day ofthe treatment. The results are shown in Table 5.

    ______________________________________                                        [Criteria of estimation]                                                      Degree of herbicidal                                                                         Herbicidal effects                                             effects        (% killed weeds)                                               ______________________________________                                        0              less than 5%                                                                  (almost no effects)                                            1               5 to 20%                                                      2              20 to 40%                                                      3              40 to 70%                                                      4              70 to 80%                                                      5              90% or more                                                                   (almost complete withering)                                    ______________________________________                                    

The % killed weeds given above was obtained from the following equationby determining the over,round raw grass weight in the phytotoxicitytreated zone and the overground raw grass weight in the untreated zone.##EQU1## Degree of phytotoxicity 0 . . . no phytotoxicity to crops

1 . . . almost no phytotoxicity to crops

2 . . . little but noticeable phytotoxicity to crops

3 . . . noticeable phytotoxicity to crops

4 . . . remarkably strong phytotoxicity to crops

5 . . . almost complete withering of crops

COMPARATIVE EXAMPLES 7 TO 12

The same procedure as in Example g was undertaken excepting the use ofthe triazine derivative A, B, C, D, E or F shown in Comparative Examples1 to 6 in place of the triazine derivative prepared in PreparationExample 1, in Example 42. The results are shown in Table 5.

    TABLE 5      Herbicidal effect      Galium  Amount of Phytotoxicity  Cassia  sparium      Compound herbicide  Grain    Abutilon Common Amaranthus obtusifolia     Ipomoea var. Veronica No. used (g/10a) Corn sorghum Wheat Barley Oats     theophrasti blackjack patulus L. purpurea echinospermon persica       Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 42 Preparation 200 0 0     0 0 0 5 5 5 5 5 5 5  Example 1 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0     0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5     5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 43 Preparation 200 0     0 0 0 0 5 5 5 5 5 5 5  Example 2 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0     0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5     5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 44 Preparation 200     0 0 0 0 0 5 5 5 5 5 5 5  Example 3 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0     0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5     5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 45 Preparation     200 0 0 0 0 0 5 5 5 5 5 5 5  Example 4 100 0 0 0 0 0 5 5 5 5 5 5 5   50     0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5     5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 46 Preparatio     n 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 5 100 0 0 0 0 0 5 5 5 5 5 5 5     50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0     5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 47     Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 6 100 0 0 0 0 0 5 5 5 5     5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0     0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 48     Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 7 100 0 0 0 0 0 5 5 5 5     5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0     0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 49     Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 8 100 0 0 0 0 0 5 5 5 5     5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0     0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 50     Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 9 100 0 0 0 0 0 5 5 5 5     5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0     0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 51     Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 10 100 0 0 0 0 0 5 5 5     5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5     0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5     52 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 11 100 0 0 0 0 0 5 5     5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5     12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5     5 5 53 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 12 100 0 0 0 0 0     5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5      12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5     5 5 5 54 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 13 100 0 0 0 0     0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5     5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5     5 5 5 5 55 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 14 100 0 0 0     0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5     5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5     5 5 5 5 5 56 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 15 100 0 0     0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5     5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5     5 5 5 5 5 5 57 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 16 100 0     0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5     5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0     5 5 5 5 5 5 5 58 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 17 100     0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5     5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0     0 5 5 5 5 5 5 5 59 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 18     100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0     5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0     0 0 0 5 5 5 5 5 5 5 60 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example     19 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0     0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0     0 0 0 0 5 5 5 5 5 5 5 61 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5     Example 20 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25     0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound     of 400 0 0 0 0 0 5 5 5 5 5 5 5 62 Preparation 200 0 0 0 0 0 5 5 5 5 5 5     5  Example 21 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5     25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example     Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 63 Preparation 200 0 0 0 0 0 5 5     5 5 5 5 5  Example 22 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5     5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5     Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 64 Preparation 200 0 0 0     0 0 5 5 5 5 5 5 5  Example 23 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0     5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5     5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 65 Preparation 200 0 0     0 0 0 5 5 5 5 5 5 5  Example 24 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0     0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5     5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 66 Preparation 200 0     0 0 0 0 5 5 5 5 5 5 5  Example 25 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0     0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5     5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 67 Preparation 200     0 0 0 0 0 5 5 5 5 5 5 5  Example 26 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0     0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5     5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 68 Preparation     200 0 0 0 0 0 5 5 5 5 5 5 5  Example 27 100 0 0 0 0 0 5 5 5 5 5 5 5   50     0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5     5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 69 Preparatio     n 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 28 100 0 0 0 0 0 5 5 5 5 5 5 5     50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0     5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 70     Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 29 100 0 0 0 0 0 5 5 5     5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5     0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5     71 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 30 100 0 0 0 0 0 5 5     5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5     12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5 5     5 5 72 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 31 100 0 0 0 0 0     5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5      12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5 5     5 5 5 73 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 32 100 0 0 0 0     0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5 5     5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5 5     5 5 5 5 74 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 33 100 0 0 0     0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5 5     5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5 5     5 5 5 5 5 75 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 34 100 0 0     0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5 5     5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0 5     5 5 5 5 5 5 76 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 35 100 0     0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5 5     5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0 0     5 5 5 5 5 5 5 77 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 36 100     0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0 5 5     5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0 0 0     0 5 5 5 5 5 5 5 78 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example 37     100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0 0     5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0 0     0 0 0 5 5 5 5 5 5 5 79 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5  Example     38 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25 0 0 0 0     0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound of 400 0     0 0 0 0 5 5 5 5 5 5 5 80 Preparation 200 0 0 0 0 0 5 5 5 5 5 5 5     Example 39 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5   25     0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example Compound     of 400 0 0 0 0 0 5 5 5 5 5 5 5 81 Preparation 200 0 0 0 0 0 5 5 5 5 5 5     5  Example 40 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5 5 5 5     25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5 Example     Compound of 400 0 0 0 0 0 5 5 5 5 5 5 5 82 Preparation 200 0 0 0 0 0 5 5     5 5 5 5 5  Example 41 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5 5 5 5     5 5 5   25 0 0 0 0 0 5 5 5 5 5 5 5   12.5 0 0 0 0 0 5 5 5 5 5 5 5     Comparative Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 Example derivative 200     0 0 0 0 0 5 5 5 5 5 5 5 7 B 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5     3 4 3 3 3 4   25 0 0 0 0 0 3 3 4 3 3 2 3   12.5 0 0 0 0 0 1 2 2 2 2 1 2     Comparative Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 Example derivative 200     0 0 0 0 0 5 5 5 5 5 5 5 8 C 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 3     3 4 4 3 3 4   25 0 0 0 0 0 3 3 4 2 3 2 3   12.5 0 0 0 0 0 2 2 2 1 2 1 2     Comparative Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 Example derivative 200     0 0 0 0 0 5 5 5 5 5 5 5 9 D 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0 0 0 5     5 5 5 4 5 5   25 0 0 0 0 0 4 4 4 4 3 4 4   12.5 0 0 0 0 0 2 2 2 2 3 3 3     Comparative Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 Example derivative 200     0 0 0 0 0 5 5 5 5 5 5 5 10 E 100 0 0 0 0 0 5 5 5 5 5 4 5   50 0 0 0 0 0     4 4 5 5 5 4 3   25 0 0 0 0 0 4 4 4 3 4 3 2   12.5 0 0 0 0 0 3 3 4 2 3 2     1 Comparative Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 Example derivative     200 0 0 0 0 0 5 5 5 5 5 5 5 11 F 100 0 0 0 0 0 5 5 5 4 5 5 5   50 0 0 0     0 0 3 5 5 3 5 3 4   25 0 0 0 0 0 3 5 5 2 5 2 3   12.5 0 0 0 0 0 1 4 5 2     3 1 2 Comparative Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 Example derivative      200 0 0 0 0 0 5 5 5 5 5 5 5 12 G 100 0 0 0 0 0 5 5 5 5 5 5 5   50 0 0 0     0 0 4 5 5 4 5 5 5   25 0 0 0 0 0 3 5 5 3 5 4 4   12.5 0 0 0 0 0 1 4 5 2     3 3 3

EXAMPLES 83 TO 123 Paddy Soil Treatment Test

Porcelain pots of 1/15500 are were filled with a paddy field soil andseeds of Echinochola crus-galli P. Beauv. var formosensis Ohwi, Cyperusdifformis L., broad-leaved weeds (Rotala indica (Willd) Koehne var.uligirosa (Miq.) Koehne and Monochoria vaginalis Presl var. plantaginea)and Scirpus juncoides Roxb. ssp. Hotarui Ohwi T. Koyama were uniformlysowed to the surface layer and further tubers of Cyperus serotinusRottb. and Sagittaria pygrmaea Miq. were transplanted followed bytransplantation of paddy rice in the bifoliate period.

Before germination of the weeds, thereafter, a specified volume of adiluted solution of the herbicide obtained in the above describedFormulation Example 6 was uniformly dropped to the water surface toeffect treatment followed by standing of the pcts in a greenhouse withperiodical sprinkling of water.

Table 6 shows the results in the investigations of the herbicidaleffects and phytotoxicity to the rice crop after 20 days from thetreatment with the herbicide solution, Incidentally, the dose is givenby the amount of the effective ingredient per 10 ares. And, thephytotoxicity to paddy rice and the herbicidal effects are expressed asshown below by determining the respective air-dried weights.

    ______________________________________                                        Extent of   Phytotoxicity to paddy rice                                       phytotoxicity                                                                             (relative to untreated zone)                                      ______________________________________                                        0           100%                                                              1           95 to 99%                                                         2           90 to 94%                                                         3           80 to 89%                                                         4           60 to 79%                                                         5           50 to 59%                                                         ______________________________________                                    

    ______________________________________                                        Degree of herbi-                                                                            Herbicidal effects (relative                                    cidal effects to untreated zone)                                              ______________________________________                                        0             100%                                                            1             61 to 99%                                                       2             21 to 60%                                                       3             11 to 20%                                                       4              1 to 10%                                                       5             0%                                                              ______________________________________                                    

COMPARATIVE EXAMPLES 13 TO 18

The same procedure as in Example 11 was undertaken excepting the use ofthe triazine derivative A, B, C, D, E or F shown in Comparative Examples1 to 6 in place of the triazine derivative prepared in PreparationExample 1, in Example 83. The results are shown in Table 6.

                                      TABLE 6                                     __________________________________________________________________________                 Amount                                                                             Herbicidal effect                                                        of   Echinochoia crus-galli                                                                   Cyperus                                                                            Scirpus juncoides                                                                      Cyperus    Sagittaria                                                                         Paddy                     Compound                                                                            herbicide                                                                          P. Beauv. var.                                                                           serotinus                                                                          Roxb. ssp. Hotarui                                                                     difformis                                                                          Broadleaf                                                                           pygmaea                                                                            rice               No.    used  (g/10a)                                                                            formosensis Ohwi                                                                         Rottb.                                                                             Ohwi T. Koyama                                                                         L.   weeds Miq. plants             __________________________________________________________________________    Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   83    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 1                                                                           12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   84    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 2                                                                           12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   85    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 3                                                                           12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   86    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 4                                                                           12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   87    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 5                                                                           12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   88    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 6                                                                           12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   89    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 7                                                                           12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   90    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 8                                                                           12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   91    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 9                                                                           12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   92    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 10                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   93    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 11                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   94    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 12                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   95    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 13                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   96    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 14                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   97    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 15                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   98    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 16                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                   99    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 17                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  100    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 18                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  101    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 19                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  102    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 20                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  103    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 21                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  104    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 22                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  105    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 23                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  106    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 24                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  107    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 25                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  108    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 26                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  109    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 27                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  110    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 28                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  111    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 29                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  112    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 30                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  113    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 31                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  114    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 32                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  115    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 33                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  116    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 34                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  117    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 35                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  118    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 36                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  119    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 37                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  120    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 38                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  121    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 39                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  122    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 40                                                                          12.5 5          5    5        5    5     5    0                  Example                                                                              Compound                                                                            100  5          5    5        5    5     5    0                  123    of    50   5          5    5        5    5     5    0                         Preparation                                                                         25   5          5    5        5    5     5    0                         Example 41                                                                          12.5 5          5    5        5    5     5    0                  Comparative                                                                          Triazine                                                                            100  5          5    5        5    5     5    0                  Example                                                                              derivative                                                                          50   5          5    4        5    4     5    0                   13    A     25   5          4    3        5    4     3    0                               12.5 5          4    2        5    4     2    0                  Comparative                                                                          Triazine                                                                            100  5          4    5        5    5     5    0                  Example                                                                              derivative                                                                          50   5          4    5        5    4     5    0                  14     B     25   5          3    4        5    4     3    0                               12.5 5          3    2        5    4     2    0                  Comparative                                                                          Triazine                                                                            100  5          5    5        5    5     5    0                  Example                                                                              derivative                                                                          50   5          5    5        5    5     5    0                  15     C     25   5          5    3        5    5     3    0                               12.5 5          3    2        5    5     3    0                  Comparative                                                                          Triazine                                                                            100  5          5    5        5    5     5    0                  Example                                                                              derivative                                                                          50   5          5    5        5    5     5    0                  16     D     25   5          5    5        5    5     5    0                               12.5 5          5    3        5    5     3    0                  Comparative                                                                          Triazine                                                                            100  5          5    5        5    5     5    0                  Example                                                                              derivative                                                                          50   5          5    5        5    5     5    0                  17     E     25   5          5    5        5    5     5    0                               12.5 5          4    3        5    5     3    0                  Comparative                                                                          Triazine                                                                            100  5          5    5        5    5     5    0                  Example                                                                              derivative                                                                          50   5          5    5        5    5     5    0                  18     F     25   5          5    5        5    5     5    0                               12.5 5          3    4        5    5     3    0                  __________________________________________________________________________

UTILIZABILITY IN INDUSTRY

The triazine derivative of the present invention is a novel compound andcan be efficiently utilized as a herbicide. The herbicide of the presentinvention with the said triazine derivative as the effective ingredientexhibits, as compared with conventional herbicides for upland field,excellent herbicidal effects against weeds including troublesome weedswithout causing phytotoxicity to upland crops and, in particular, aremarkably high effect can be obtained by the treatment to the soilbefore preemergence or by the treatment to foliage in the fields ofcrops belonging to Gramineous crops. Further, the herbicides of thepresent invention exhibit higher effectiveness against troublesome weedsstill with less phytotoxicity than hitherto known herbicides for paddyrice.

We claim:
 1. A triazine compound of the formula ##STR61## wherein Y¹ isa hydrogen atom or a methyl group and Z is an oxygen atom or a sulfuratom, X¹ is a halogen atom and R¹ is a hydrogen atom, a methyl group oran ethyl group, excluding the compound where Y¹ is hydrogen, R¹ ishydrogen and X¹ is chlorine.
 2. The triazine compound of claim 1,wherein Z is a sulfur atom.
 3. The triazine compound of claim 1, whereinZ is an oxygen atom.
 4. The triazine compound of claim 1, wherein X¹ isa fluorine atom or a chlorine atom, R¹ is hydrogen or a methyl group. 5.The triazine compound of claim 1, wherein the compound is selected fromthe group consistingof2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-fluoro, α-methylethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-chloro, α-methylethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-bromo, α-methylethyl)-s-triazine.2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-fluoroethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-fluoro, α-methylpropyl)-s-triazine. 2-amino-4-[1-(benzothiophen-2'-yl)ethylamino]-6-(α-fluoro, α-methyl ethyl)-s-triazine;2-amino-4-[1-(benzothiophen-2'-yl)ethylamino]-6-(α-chloro, α-methylethyl)-s-triazine;2-amino-4-[1-(benzothiophen-2'-yl)ethylamino]-6-(α-fluoroethyl)-s-triazine;2-amino-4-[1-(6'-methylbenzofuran-2'-yl)ethylamino]-6-(α-fluoro,α-methyl ethyl)-s-triazine;2-amino-4-[1-(6'-methylbenzofuran-2'-yl)ethylamino]-6-(α-fluoroethyl)-s-triazine and2-amino-4-[1-6'-methylbenzofuran-2'-yl)ethylamino]-6-(α-chloro, α-methylethyl)-s-triazine.
 6. A herbicidal composition comprising an effectiveherbicidal amount of a triazine compound of claim 1 in admixture with acarrier.
 7. The herbicidal composition according to claim 6, wherein thetriazine compound is selected from the group consistingof2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-fluoro, α-methylethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-chloro, α-methylethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-bromo, α-methylethyl)-s-triazine.2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-fluoroethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-fluoro, α-methylpropyl)-s-triazine.2-amino-4-[1-(benzothiophen-2'-yl)ethylamino]-6-(α-fluoro, α-methylethyl)-s-triazine.2-amino-4-[1-(benzothiophen-2'-yl)ethylamino]-6-(α-chloro, α-methylethyl)-s-triazine;2-amino-4-[1-(benzothiophen-2'-yl)ethylamino]-6-(α-fluoroethyl)-s-triazine;2-amino-4-[1-(6'-methylbenzofuran-2'-yl)ethylamino]-6-(α-fluoro,α-methyl ethyl)-s-triazine;2-amino-4-[1-(6'-methylbenzofuran-2'-yl)ethylamino]-6-(α-fluoroethyl)-s-triazine and2-amino-4-[1-6'-methylbenzofuran-2'-yl)ethylamino]-6-(α-chloro, α-methylethyl)-s-triazine.
 8. A method of combatting weeds comprising applyingto weeds or to a locus thereof an effective herbicidal amount of atriazine compound of claim
 1. 9. The method of combatting weedsaccording to claim 8, wherein the triazine compound is selected from thegroup consistingof2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-fluoro, α-methylethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-chloro, α-methylethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-bromo, α-methylethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-fluoroethyl)-s-triazine;2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-fluoro, α-methylpropyl)-s-triazine;2-amino-4-[1-(benzothiophen-2'-yl)ethylamino]-6-(α-fluoro, α-methylethyl)-s-triazine.2-amino-4-[1-(benzothiophen-2'-yl)ethylamino]-6-(α-chloro, α-methylethyl)-s-triazine;2-amino-4-[1-(benzothiophen-2'-yl)ethylamino]-6-(α-fluoroethyl)-s-triazine;2-amino-4-[1-(6'-methylbenzofuran-2'-yl)ethylamino]-6-(α-fluoro,α-methyl ethyl)-s-triazine;2-amino-4-[1-(6'-methylbenzofuran-2'-yl)ethylamino]-6-(α-fluoroethyl)-s-triazineand 2-amino-4-[1-6'-methylbenzofuran-2'-yl)ethylamino]-6-(α-chloro,α-methyl ethyl)-s-triazine.
 10. The method of combatting weeds accordingto claim 9, wherein said triazine compound is applied to a soil surfacein an amount of 1 g/1 ares to 100 g/10 ares.
 11. The method ofcombatting weeds according to claim 9, wherein the weeds are selectedfrom the group consisting of Alopecurus myosuroides, Digitariasanguinalis, Abutilon theophrasti, Veronica persica, Polygonumpersicaria, Viola arvensis, Amaranthus patulus and Galium sparium var.echinospermon.
 12. The method of combatting weeds according to claim 9,wherein said triazine compound is applied to a soil surface in an amountof 1 g/10 to 100 g/10 ares and the weeds are selected from the groupconsisting of Alopecurus myosuroides, Digitaria Sanguinalis, Abutilontheophrasti, Veronica persica, Polygonum persicaria, Viola arvensis,Amaranthus patulus and Galium sparium var. echinospermon.
 13. Thetriazine compound of claim 1, wherein R¹ is a methyl group.
 14. Thetriazine compound of claim 1, wherein R¹ is an ethyl group.
 15. Thetriazine compound of claim 1, wherein Y¹ is a methyl group.
 16. Thetriazine compound of claim 15, wherein Z is a sulfur atom. 17.2-Amino-4-[-benzofuran-2'-yl)ethylamino]-6-(α-chloroethyl)-s-triazine.18. A herbicidal composition comprising an effective herbicidal amountof2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-chloroethyl)-s-triazinein admixture with a carrier.
 19. A method of combatting weeds comprisingapplying to weeds or to a locus thereof an effective herbicidal amountof2-amino-4-[1-(benzofuran-2'-yl)ethylamino]-6-(α-chloroethyl)-s-triazine.20. The method of combatting weeds according to claim 19, wherein saidtriazine is applied to a soil surface in an amount of 1 g/1 ares to 100g/10 ares.
 21. The method of combatting weeds according to claim 19,wherein the weeds are selected from the group consisting of Alopecurusmyosuroides, Digitaria sanguinalis, Abutilon theophrasti, Veronicapersica, Polygonum persicaria, Viola arvensis, Amaranthus patulus andGalium sparium var. echinospermon.
 22. The method of combatting weedsaccording to claim 19, wherein said triazine is applied to a soilsurface in an amount of 1 g/10 to 100 g/10 ares and the weeds areselected from the group consisting of Alopecurus myosuroides, DigitariaSanguinalis, Abutilon theophrasti, Veronica persica, Polygonumpersicaria, Viola arvensis, Amaranthus patulus and Galium sparium var.echinospermon.